#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:28:13 +0300 (Fri, 05 May 2023) $
#$Revision: 283487 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159219.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159219
loop_
_publ_author_name
'Liu, Donghan'
'Song, Siyu'
'Chen, Longkun'
'Zhang, Mingshuai'
'Liu, Zhuoyuan'
'Lu, Xihang'
'Huang, Jiuzhong'
'Yu, Fuchao'
_publ_section_title
;
 Access to thiionized-, selenolized-, and alkylated 5-alkylidene
 3-pyrrolin-2-one derivatives via a regioselective oxidative
 annulation reaction.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2596
_journal_page_last               2602
_journal_paper_doi               10.1039/d3ob00014a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H18 N2 O'
_chemical_formula_sum            'C19 H18 N2 O'
_chemical_formula_weight         290.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-15 deposited with the CCDC.	2023-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.346(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.578(6)
_cell_length_b                   10.373(5)
_cell_length_c                   13.434(6)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.48
_cell_volume                     1612.1(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_unetI/netI     0.1011
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9310
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.620
_diffrn_reflns_theta_min         2.637
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0897 before and 0.0543 after correction.
The Ratio of minimum to maximum transmission is 0.6921.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.1652
_refine_ls_R_factor_gt           0.0807
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1141P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.2296
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1666
_reflns_number_total             3638
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00014a2.cif
_cod_data_source_block           221209yfc50_0m
_cod_depositor_comments
'Adding full bibliography for 7159219--7159221.cif.'
_cod_original_cell_volume        1612.0(13)
_cod_database_code               7159219
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), C009(H009), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00I(H00J), C00L(H00M)
2.b X=CH2 refined with riding coordinates:
 C00K(H00K,H00L)
2.c Idealised Me refined as rotating group:
 C00H(H00B,H00H,H00I), C00M(H00N,H00O,H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.61688(17) 0.0715(2) 0.46403(13) 0.0587(6) Uani 1 1 d . . . . .
N002 N 0.6874(2) 0.2770(2) 0.44040(16) 0.0537(6) Uani 1 1 d . . . . .
N003 N 0.47963(19) 0.1801(2) 0.61270(15) 0.0544(6) Uani 1 1 d . . . . .
H003 H 0.473524 0.100727 0.594697 0.065 Uiso 1 1 calc R U . . .
C004 C 0.6200(2) 0.1862(3) 0.48319(18) 0.0467(7) Uani 1 1 d . . . . .
C005 C 0.4114(2) 0.2180(2) 0.69191(18) 0.0478(7) Uani 1 1 d . . . . .
C006 C 0.5545(2) 0.2538(3) 0.56078(18) 0.0487(7) Uani 1 1 d . . . . .
C007 C 0.2700(3) 0.2872(3) 0.84879(19) 0.0549(8) Uani 1 1 d . . . . .
C008 C 0.7622(2) 0.2511(3) 0.36072(19) 0.0540(8) Uani 1 1 d . . . . .
C009 C 0.3678(3) 0.3551(3) 0.8298(2) 0.0591(8) Uani 1 1 d . . . . .
H009 H 0.387055 0.425755 0.869689 0.071 Uiso 1 1 calc R U . . .
C00A C 0.3155(3) 0.1463(3) 0.7119(2) 0.0611(8) Uani 1 1 d . . . . .
H00A H 0.297180 0.074083 0.673405 0.073 Uiso 1 1 calc R U . . .
C00B C 0.6685(3) 0.3996(3) 0.4846(2) 0.0602(8) Uani 1 1 d . . . . .
C00C C 0.4396(3) 0.3227(3) 0.7533(2) 0.0607(8) Uani 1 1 d . . . . .
H00C H 0.506026 0.370581 0.743039 0.073 Uiso 1 1 calc R U . . .
C00D C 0.5851(3) 0.3778(3) 0.5602(2) 0.0606(8) Uani 1 1 d . . . . .
H00D H 0.557032 0.440871 0.602092 0.073 Uiso 1 1 calc R U . . .
C00E C 0.2457(3) 0.1807(3) 0.7892(2) 0.0657(9) Uani 1 1 d . . . . .
H00E H 0.180978 0.130959 0.801278 0.079 Uiso 1 1 calc R U . . .
C00F C 0.8429(3) 0.1555(3) 0.3694(2) 0.0669(9) Uani 1 1 d . . . . .
H00F H 0.850204 0.108053 0.428056 0.080 Uiso 1 1 calc R U . . .
C00G C 0.7514(3) 0.3206(3) 0.2727(2) 0.0724(9) Uani 1 1 d . . . . .
H00G H 0.695246 0.384398 0.264982 0.087 Uiso 1 1 calc R U . . .
C00H C 0.1931(3) 0.3252(3) 0.9322(2) 0.0724(9) Uani 1 1 d . . . . .
H00B H 0.237066 0.323789 0.994354 0.109 Uiso 1 1 calc R U . . .
H00H H 0.129970 0.265521 0.935000 0.109 Uiso 1 1 calc R U . . .
H00I H 0.163469 0.410499 0.920211 0.109 Uiso 1 1 calc R U . . .
C00I C 0.9140(3) 0.1282(4) 0.2919(2) 0.0813(11) Uani 1 1 d . . . . .
H00J H 0.967631 0.061782 0.298774 0.098 Uiso 1 1 calc R U . . .
C00J C 0.9066(3) 0.1982(5) 0.2042(2) 0.0896(12) Uani 1 1 d . . . . .
C00K C 0.7197(3) 0.5080(3) 0.4612(3) 0.0875(11) Uani 1 1 d . . . . .
H00K H 0.773576 0.508794 0.411751 0.105 Uiso 1 1 calc R U . . .
H00L H 0.701929 0.583938 0.494103 0.105 Uiso 1 1 calc R U . . .
C00L C 0.8244(3) 0.2945(4) 0.1966(2) 0.0889(12) Uani 1 1 d . . . . .
H00M H 0.817954 0.343132 0.138447 0.107 Uiso 1 1 calc R U . . .
C00M C 0.9862(4) 0.1691(6) 0.1203(3) 0.147(2) Uani 1 1 d . . . . .
H00N H 1.064607 0.187005 0.141793 0.220 Uiso 1 1 calc R U . . .
H00O H 0.965206 0.221873 0.063679 0.220 Uiso 1 1 calc R U . . .
H00P H 0.979097 0.079796 0.102123 0.220 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C004 N002 C008 124.0(2) . . ?
C004 N002 C00B 109.9(2) . . ?
C00B N002 C008 126.0(2) . . ?
C005 N003 H003 116.0 . . ?
C006 N003 H003 116.0 . . ?
C006 N003 C005 128.0(2) . . ?
O001 C004 N002 126.7(2) . . ?
O001 C004 C006 126.6(2) . . ?
N002 C004 C006 106.6(2) . . ?
C00A C005 N003 118.7(2) . . ?
C00A C005 C00C 118.6(3) . . ?
C00C C005 N003 122.7(3) . . ?
N003 C006 C004 116.4(2) . . ?
C00D C006 N003 135.7(3) . . ?
C00D C006 C004 107.8(2) . . ?
C009 C007 C00E 116.9(3) . . ?
C009 C007 C00H 121.5(3) . . ?
C00E C007 C00H 121.6(3) . . ?
C00F C008 N002 120.5(3) . . ?
C00F C008 C00G 119.3(3) . . ?
C00G C008 N002 120.3(3) . . ?
C007 C009 H009 118.7 . . ?
C007 C009 C00C 122.7(3) . . ?
C00C C009 H009 118.7 . . ?
C005 C00A H00A 119.7 . . ?
C005 C00A C00E 120.5(3) . . ?
C00E C00A H00A 119.7 . . ?
N002 C00B C00D 105.8(2) . . ?
C00K C00B N002 125.8(3) . . ?
C00K C00B C00D 128.4(3) . . ?
C005 C00C H00C 120.2 . . ?
C009 C00C C005 119.5(3) . . ?
C009 C00C H00C 120.2 . . ?
C006 C00D C00B 109.8(3) . . ?
C006 C00D H00D 125.1 . . ?
C00B C00D H00D 125.1 . . ?
C007 C00E C00A 121.8(3) . . ?
C007 C00E H00E 119.1 . . ?
C00A C00E H00E 119.1 . . ?
C008 C00F H00F 119.6 . . ?
C008 C00F C00I 120.7(3) . . ?
C00I C00F H00F 119.6 . . ?
C008 C00G H00G 120.2 . . ?
C00L C00G C008 119.5(3) . . ?
C00L C00G H00G 120.2 . . ?
C007 C00H H00B 109.5 . . ?
C007 C00H H00H 109.5 . . ?
C007 C00H H00I 109.5 . . ?
H00B C00H H00H 109.5 . . ?
H00B C00H H00I 109.5 . . ?
H00H C00H H00I 109.5 . . ?
C00F C00I H00J 119.4 . . ?
C00F C00I C00J 121.1(4) . . ?
C00J C00I H00J 119.4 . . ?
C00I C00J C00M 120.7(4) . . ?
C00L C00J C00I 117.4(3) . . ?
C00L C00J C00M 121.9(4) . . ?
C00B C00K H00K 120.0 . . ?
C00B C00K H00L 120.0 . . ?
H00K C00K H00L 120.0 . . ?
C00G C00L C00J 121.9(3) . . ?
C00G C00L H00M 119.0 . . ?
C00J C00L H00M 119.0 . . ?
C00J C00M H00N 109.5 . . ?
C00J C00M H00O 109.5 . . ?
C00J C00M H00P 109.5 . . ?
H00N C00M H00O 109.5 . . ?
H00N C00M H00P 109.5 . . ?
H00O C00M H00P 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C004 1.218(3) . ?
N002 C004 1.365(3) . ?
N002 C008 1.430(3) . ?
N002 C00B 1.424(4) . ?
N003 H003 0.8600 . ?
N003 C005 1.407(3) . ?
N003 C006 1.368(3) . ?
C004 C006 1.490(4) . ?
C005 C00A 1.372(4) . ?
C005 C00C 1.394(4) . ?
C006 C00D 1.334(4) . ?
C007 C009 1.366(4) . ?
C007 C00E 1.387(4) . ?
C007 C00H 1.512(4) . ?
C008 C00F 1.364(4) . ?
C008 C00G 1.387(4) . ?
C009 H009 0.9300 . ?
C009 C00C 1.390(4) . ?
C00A H00A 0.9300 . ?
C00A C00E 1.388(4) . ?
C00B C00D 1.447(4) . ?
C00B C00K 1.315(4) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.382(4) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.380(4) . ?
C00H H00B 0.9600 . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00I H00J 0.9300 . ?
C00I C00J 1.383(5) . ?
C00J C00L 1.381(5) . ?
C00J C00M 1.515(5) . ?
C00K H00K 0.9300 . ?
C00K H00L 0.9300 . ?
C00L H00M 0.9300 . ?
C00M H00N 0.9600 . ?
C00M H00O 0.9600 . ?
C00M H00P 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C004 C006 N003 -3.0(4) . . . . ?
O001 C004 C006 C00D 177.9(3) . . . . ?
N002 C004 C006 N003 179.2(2) . . . . ?
N002 C004 C006 C00D 0.1(3) . . . . ?
N002 C008 C00F C00I 178.7(3) . . . . ?
N002 C008 C00G C00L 179.9(3) . . . . ?
N002 C00B C00D C006 -1.0(3) . . . . ?
N003 C005 C00A C00E -179.8(3) . . . . ?
N003 C005 C00C C009 179.7(3) . . . . ?
N003 C006 C00D C00B -178.3(3) . . . . ?
C004 N002 C008 C00F -54.0(4) . . . . ?
C004 N002 C008 C00G 124.2(3) . . . . ?
C004 N002 C00B C00D 1.1(3) . . . . ?
C004 N002 C00B C00K 179.7(3) . . . . ?
C004 C006 C00D C00B 0.6(3) . . . . ?
C005 N003 C006 C004 177.1(2) . . . . ?
C005 N003 C006 C00D -4.0(5) . . . . ?
C005 C00A C00E C007 -0.3(5) . . . . ?
C006 N003 C005 C00A 158.2(3) . . . . ?
C006 N003 C005 C00C -24.2(4) . . . . ?
C007 C009 C00C C005 0.8(5) . . . . ?
C008 N002 C004 O001 3.4(4) . . . . ?
C008 N002 C004 C006 -178.8(2) . . . . ?
C008 N002 C00B C00D 179.1(2) . . . . ?
C008 N002 C00B C00K -2.3(5) . . . . ?
C008 C00F C00I C00J 1.0(5) . . . . ?
C008 C00G C00L C00J 1.8(5) . . . . ?
C009 C007 C00E C00A -1.7(5) . . . . ?
C00A C005 C00C C009 -2.8(4) . . . . ?
C00B N002 C004 O001 -178.5(3) . . . . ?
C00B N002 C004 C006 -0.7(3) . . . . ?
C00B N002 C008 C00F 128.3(3) . . . . ?
C00B N002 C008 C00G -53.5(4) . . . . ?
C00C C005 C00A C00E 2.6(4) . . . . ?
C00E C007 C009 C00C 1.5(5) . . . . ?
C00F C008 C00G C00L -1.9(5) . . . . ?
C00F C00I C00J C00L -1.1(5) . . . . ?
C00F C00I C00J C00M 179.0(4) . . . . ?
C00G C008 C00F C00I 0.5(5) . . . . ?
C00H C007 C009 C00C -179.6(3) . . . . ?
C00H C007 C00E C00A 179.3(3) . . . . ?
C00I C00J C00L C00G -0.3(5) . . . . ?
C00K C00B C00D C006 -179.6(3) . . . . ?
C00M C00J C00L C00G 179.6(4) . . . . ?
